US9751973B2 - Epoxy systems for composites - Google Patents
Epoxy systems for composites Download PDFInfo
- Publication number
- US9751973B2 US9751973B2 US15/060,411 US201615060411A US9751973B2 US 9751973 B2 US9751973 B2 US 9751973B2 US 201615060411 A US201615060411 A US 201615060411A US 9751973 B2 US9751973 B2 US 9751973B2
- Authority
- US
- United States
- Prior art keywords
- group
- epoxy resin
- amine
- amine compound
- combinations
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
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- 239000004593 Epoxy Substances 0.000 title claims description 29
- 239000002131 composite material Substances 0.000 title abstract description 31
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 137
- 239000003822 epoxy resin Substances 0.000 claims abstract description 132
- -1 amine compound Chemical class 0.000 claims abstract description 122
- 239000000203 mixture Substances 0.000 claims abstract description 118
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 79
- 238000000034 method Methods 0.000 claims abstract description 37
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 29
- 125000000524 functional group Chemical group 0.000 claims abstract description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 22
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 17
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 12
- 150000003512 tertiary amines Chemical group 0.000 claims description 44
- 150000003141 primary amines Chemical group 0.000 claims description 35
- 239000000835 fiber Substances 0.000 claims description 30
- 150000003335 secondary amines Chemical group 0.000 claims description 27
- 239000000758 substrate Substances 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 20
- 229920005862 polyol Polymers 0.000 claims description 20
- 150000003077 polyols Chemical class 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 19
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 17
- 150000004985 diamines Chemical class 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 14
- 238000001802 infusion Methods 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 12
- 229920000570 polyether Polymers 0.000 claims description 12
- 239000012783 reinforcing fiber Substances 0.000 claims description 12
- 239000011152 fibreglass Substances 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 8
- 239000010695 polyglycol Substances 0.000 claims description 8
- 229920000151 polyglycol Polymers 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229920000058 polyacrylate Polymers 0.000 claims description 6
- 229920000193 polymethacrylate Polymers 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 2
- 229910001593 boehmite Inorganic materials 0.000 claims description 2
- 235000010216 calcium carbonate Nutrition 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims description 2
- 229910052570 clay Inorganic materials 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 235000010755 mineral Nutrition 0.000 claims description 2
- 238000000465 moulding Methods 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 23
- 238000004519 manufacturing process Methods 0.000 abstract description 12
- 125000002723 alicyclic group Chemical group 0.000 abstract description 4
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 abstract 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 1
- 229920005989 resin Polymers 0.000 description 74
- 239000011347 resin Substances 0.000 description 74
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 40
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 21
- 150000001412 amines Chemical class 0.000 description 17
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical group CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 15
- 239000003085 diluting agent Substances 0.000 description 14
- 230000009477 glass transition Effects 0.000 description 14
- 239000004743 Polypropylene Substances 0.000 description 13
- 238000009472 formulation Methods 0.000 description 13
- YSAANLSYLSUVHB-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]ethanol Chemical compound CN(C)CCOCCO YSAANLSYLSUVHB-UHFFFAOYSA-N 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 12
- 239000004744 fabric Substances 0.000 description 12
- YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 description 12
- 229920001155 polypropylene Polymers 0.000 description 12
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 238000011161 development Methods 0.000 description 11
- 229920001971 elastomer Polymers 0.000 description 11
- 239000005060 rubber Substances 0.000 description 11
- HSDVRWZKEDRBAG-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COC(CCCCC)OCC1CO1 HSDVRWZKEDRBAG-UHFFFAOYSA-N 0.000 description 10
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 10
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 0 [1*]N([2*])[3*] Chemical compound [1*]N([2*])[3*] 0.000 description 9
- 150000002170 ethers Chemical class 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- 238000007373 indentation Methods 0.000 description 8
- HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 7
- FLCAEMBIQVZWIF-UHFFFAOYSA-N 6-(dimethylamino)-2-methylhex-2-enamide Chemical compound CN(C)CCCC=C(C)C(N)=O FLCAEMBIQVZWIF-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 239000011258 core-shell material Substances 0.000 description 6
- 150000002334 glycols Chemical class 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 229920000768 polyamine Polymers 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- FBHPRUXJQNWTEW-UHFFFAOYSA-N 1-benzyl-2-methylimidazole Chemical compound CC1=NC=CN1CC1=CC=CC=C1 FBHPRUXJQNWTEW-UHFFFAOYSA-N 0.000 description 5
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical group CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 239000012745 toughening agent Substances 0.000 description 5
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 239000008199 coating composition Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- UQKAOOAFEFCDGT-UHFFFAOYSA-N n,n-dimethyloctan-1-amine Chemical compound CCCCCCCCN(C)C UQKAOOAFEFCDGT-UHFFFAOYSA-N 0.000 description 4
- 239000002121 nanofiber Substances 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 4
- 229910010271 silicon carbide Inorganic materials 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- 229910002804 graphite Inorganic materials 0.000 description 3
- 239000010439 graphite Substances 0.000 description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002086 nanomaterial Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 229920003048 styrene butadiene rubber Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229960001124 trientine Drugs 0.000 description 3
- 150000004072 triols Chemical class 0.000 description 3
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 2
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 2
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 238000006683 Mannich reaction Methods 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 238000009730 filament winding Methods 0.000 description 2
- 229920002457 flexible plastic Polymers 0.000 description 2
- 230000020169 heat generation Effects 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 229940031826 phenolate Drugs 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000012779 reinforcing material Substances 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 2
- 239000012815 thermoplastic material Substances 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 238000001721 transfer moulding Methods 0.000 description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
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- C—CHEMISTRY; METALLURGY
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- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
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- C08G59/50—Amines
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
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- C—CHEMISTRY; METALLURGY
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/56—Amines together with other curing agents
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Abstract
Description
wherein R1 and R2 each comprise an organic functional group having from 1-6 carbon atoms, and R3 comprises an alkyl group, having a backbone of 2-18 carbon atoms and a second amine compound having one or more primary or secondary amine groups, wherein the stoichiometic ratio of the —NH bonds of the second amine compound to the epoxy groups of the epoxy resin component is from about 1:20 to about 21:20 and the molar ratio of the second amine compound to the first amine compound is from about 0.01:1 to about 100:1.
wherein R1 and R2 each comprise an organic functional group having from 1-6 carbon atoms, and R3 comprises an alkyl group, having a backbone of 2-18 carbon atoms and a second amine compound having one or more primary or secondary amine groups, wherein the stoichiometic ratio of the —NH bonds of the second amine compound to the epoxy groups of the epoxy resin component is from about 1:20 to about 21:20 and molar ratio of the second amine compound to the first amine compound is from about 0.01:1 to about 100:1.
wherein R1 and R2 each comprise an organic functional group having from 1-6 carbon atoms, and R3 comprises an alkyl group, having a backbone of 2-18 carbon atoms and a second amine compound having one or more primary or secondary amine groups, wherein the stoichiometic ratio of the —NH bonds of the second amine compound to the epoxy groups of the epoxy resin component is from about 1:20 to about 21:20 and molar ratio of the second amine compound to the first amine compound is from about 0.01:1 to about 100:1, and reacting the epoxy resin component and curing agent.
wherein R1 and R2 each comprise an organic functional group having from 1-6 carbon atoms, and R3 comprises an alkyl group, having a backbone of 2-18 carbon atoms, and a second amine compound having one or more primary or secondary amine groups, wherein the stoichiometic ratio of the —NH bonds of the second amine compound to the epoxy groups of the epoxy resin component is from about 1:20 to about 21:20 and molar ratio of the second amine compound to the first amine compound is from about 0.01:1 to about 100:1, contacting the reinforcing fiber substrate with the epoxy resin system, and curing the epoxy resin system to form the composite.
and R1 and R2 groups may each be, independently, an organic functional group having from 1-6 carbon atoms. The organic functional group may be an aliphatic or an alicyclic organic functional group. Alternatively, R1 and R2 may comprise one common ring. The R3 group may be an alkyl group, having a backbone of 2-18 carbon atoms, such as from 4-12 carbon atoms, or in one example, from 8-18 carbon atoms.
R1 and R2 groups may each be, independently, an organic functional group having from 1-6 carbon atoms, such as an aliphatic organic group, an alicyclic organic group, or combinations thereof. Examples of aliphatic groups include alkyl groups selected from the group of a methyl group, an ethyl group, and a propyl group. The alicyclic organic group may include, for example, a C5-C6 carbocyclic aliphatic ring, a C5-C6 heterocyclic aliphatic ring, a C5-C6 saturated aliphatic ring, or a C5-C6 unsaturated aliphatic ring. Alternatively, R1 and R2 may jointly comprise one common ring, and R3 may have one carbon atom, such as a methyl group when R1 and R2 jointly comprise one common ring.
with Me representing a methyl group and the R3 group being an aliphatic linear alkyl group having a backbone of 8-12 carbon atoms as described herein.
TABLE 1 |
Cure of a diluted EPON Resin 828 with Various Primary and Tertiary Amines |
Mixture# |
1 (control) | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | ||
EPON Resin | 6.16 | 6.16 | 6.16 | 6.16 | 6.16 | 6.16 | 6.16 | 6.16 | 6.16 | 6.16 |
828, g | ||||||||||
HDDGE, g | 1.54 | 1.54 | 1.54 | 1.54 | 1.54 | 1.54 | 1.54 | 1.54 | 1.54 | 1.54 |
(diluent) | ||||||||||
IPDA, g | 0.92 | 0.62 | 0.62 | 0.31 | 0.31 | 0.31 | 0.64 | 0 | 0 | 0 |
Jeffamine D- | 1.39 | 0.92 | 0.92 | 0.46 | 0.46 | 0.46 | 0 | 0.90 | 0 | 0 |
230, g | ||||||||||
NH/epoxy | 1.0 | 0.68 | 0.68 | 0.34 | 0.34 | 0.34 | 0.34 | 0.34 | 0 | 0 |
ratio | ||||||||||
Tetramethyl- | 0 | 0.27 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
guanidine | ||||||||||
(TMG), g | ||||||||||
DDMA, |
0 | 0 | 0.27 | 0.27 | 0.40 | 0.54 | 0.54 | 0.54 | 0.54 | 0.81 |
Did PP beaker | Yes | N/A | N/A | No | No | No | No | No | No | No |
melt? | ||||||||||
Shrinkage | Yes | N/A | N/A | No | No | No | No | No | No | No |
indentations in | ||||||||||
cured sample? | ||||||||||
Tg, ° C., after | ||||||||||
cure time at | ||||||||||
70° C.: | ||||||||||
2 hours | 51 | 43 | 55 | 38 | 52 | 59 | N/A | 54 | 43 | 47 |
3 |
65 | 77 | 73 | 45 | 64 | 77 | N/ |
55 | 49 | 74 |
4 hours | 72 | 82 | 77 | 51 | 75 | 80 | N/A | 67 | 60 | 78 |
5 |
77 | 84 | 81 | 55 | 81 | 83 | N/ |
74 | 77 | 80 |
6 hours | 80 | N/A | 83 | 70 | 83 | 85 | N/ |
76 | 78 | 82 |
6 hours (repeat | 77 | N/A | 86 | 75 | 81 | 89 | 91 | 76 | 79 | 83 |
cure) |
Cure on 100 gram mass in 70° C. water bath: |
Max peak | 261 | 275 | 233 | 188 | 200 | 208 | N/A | 204 | 172 | 191 |
exotherm temp | ||||||||||
at center, ° C. | ||||||||||
Time to max | 18 | 25 | 22 | 29 | 28 | 29 | N/A | 27 | 36 | 35 |
peak | ||||||||||
temperature, | ||||||||||
min |
Tensile properties: |
Yield strength, | 66.2 | N/A | 64.3 | 56.5 | 63.4 | 61.3 | N/A | 58.4 | 55.5 | N/A |
MPa | ||||||||||
Modulus, MPa | 2953 | N/A | 2663 | 2629 | 2677 | 2551 | N/A | 2517 | 2423 | N/A |
Elongation at | 9.7 | N/A | 10.7 | 14.2 | 10.5 | 10.7 | N/A | 8.6 | 10.9 | N/A |
break, % | ||||||||||
TABLE 2 |
Cure of a diluted EPON Resin 828 with Various Primary and |
Tertiary Amines |
1 (con- | |||||
Mixture# | trol) | 2 | 3 | 4 | 5 |
EPON Resin 828 and | 100 | 100 | 100 | 100 | 100 |
HDDGE (diluent), parts | |||||
Jeffamine D-230, parts | 18 | 12 | 9 | 6 | 6 |
IPDA, parts | 12 | 8 | 6 | 4 | 4 |
Tetramethylguanidine | 0 | 3.5 | 0 | 0 | 0 |
(TMG), parts | |||||
DDMA, parts | 0 | 0 | 6 | 0 | 0 |
DMA, parts | 0 | 0 | 0 | 6 | 0 |
DMAEE, parts | 0 | 0 | 0 | 0 | 3.4 |
Tg, ° C., after cure time at | |||||
70° C.: | |||||
2 hours | 51 | 43 | 68 | 74 | 78 |
3 hours | 65 | 77 | 78 | 80 | N/A |
4 hours | 72 | 82 | 82 | 84 | 88 |
5 hours | 77 | 84 | 86 | 85 | 88 |
6 hours | 80 | N/A | 87 | 87 | 92 |
6 hours (repeat cure) | 77 | 87 | 87 | 87 | 89 |
Tg, ° C., after 6 hours at | 88.5 | 85.2 | 80.7 | 82.4 | 94 |
70° C. cure and after 30 | |||||
min at 200° C.: | |||||
Max peak exotherm temp | 261 | 275 | 228 | 218 | 208 |
at center, ° C.* | |||||
Time to max peak | 18 | 27 | 22 | 26 | 24 |
temperature, min | |||||
Viscosity, Brookfield, | 311 | 279 | 276 | 342 | N/A |
25° C., mPa-s (cps) | |||||
Tensile properties: | |||||
Yield strength, MPa | 66.2 | 69.8 | 62.9 | 60.9 | N/A |
Break strength, MPa | N/A | N/A | 54.7 | 43.3 | N/A |
Modulus, MPa | 2953 | 2961 | 2718 | 3342 | N/A |
Yield strain, % | 4.5 | 5.0 | 5.0 | 3.3 | N/A |
Break strain, % | 9.7 | 9.8 | 9.4 | 10.9 | N/A |
*Cure on 100 gram mass in 70° C. water bath. |
TABLE 3A |
Cure of Diluted EPON Resin 828 with Mixtures of Primary Amines with Tertiary Amines or |
Other “Catalytic” Curing Agents, Samples 1-8 |
Mixture# |
Control 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | ||
80% EPON Resin 828/ | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 |
20% HDDGE (diluent) | ||||||||
mixture, parts | ||||||||
Jeffamine D-230, parts | 18 | 6 | 6 | 6 | 6 | 6 | 6 | 6 |
IPDA, parts | 12 | 4 | 4 | 4 | 4 | 4 | 4 | 4 |
N—H/epoxy ratio | 1.00 | 0.33 | 0.33 | 0.33 | 0.33 | 0.33 | 0.33 | 0.33 |
DDMA, parts | 0 | 3.5 | 5.2 | 7.0 | 0 | 0 | 0 | 0 |
DMA, parts | 0 | 0 | 0 | 0 | 4.5 | 6.1 | 9.1 | 0 |
DMAEE, parts | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 3.4 |
TMG, parts | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
1-Bz-2-MI, parts | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
Tg, ° C., after cure time | ||||||||
Fat 70° C.: | ||||||||
2 hours | 51 | 38 | 52 | 59 | 54 | 74 | N/A | 78 |
3 hours | 65 | 45 | 64 | 77 | 73 | 80 | N/A | N/A |
4 hours | 72 | 51 | 75 | 80 | 82 | 84 | N/A | 88 |
5 hours | 77 | 55 | 81 | 83 | 85 | 85 | N/A | 88 |
6 hours | 80 | 70 | 83 | 85 | 85 | 87 | N/A | 92 |
6 hours (repeat cure) | 77 | 75 | 81 | 89 | 86 | 87 | 82 | 89 |
Tg, ° C., after 6 hours | 88.5 | 80 | 82 | 79 | 86 | 82 | 71 | 94 |
at 70° C. cure and after | ||||||||
30 min at 200° C.: | ||||||||
Max peak exotherm | 261 | 188 | 200 | 208 | 208 | 218 | N/A | 208 |
temp at center, ° C.* | ||||||||
Time to max peak | 18 | 29 | 28 | 29 | 23 | 24 | N/A | 24 |
temperature, min* | ||||||||
Viscosity, Brookfield, | 203 | 312 | 269 | 240 | N/A | N/A | N/A | 362 |
30° C., mPa-s (cp) | ||||||||
Yield strength, MPa | 66.2 | 56.5 | 63.4 | 61.3 | N/A | 60.9 | N/A | N/A |
Break strength, MPa | N/A | 47.2 | 57 | 54.4 | N/A | 43.3 | N/A | N/A |
Modulus, MPa | 2953 | 2629 | 2677 | 2551 | N/A | 3342 | N/A | N/A |
Yield strain, % | 4.5 | 4.4 | 5.4 | 5.6 | N/A | 3.3 | N/A | N/A |
Break strain, % | 9.7 | 14.2 | 10.5 | 10.7 | N/A | 10.9 | N/A | N/A |
*Cure on 100 gram mass in 70° C. water bath. |
Table 3B |
Cure of Diluted EPON Resin 828 with Mixtures of Primary |
Amines with Tertiary Amines or Other “Catalytic” |
Curing Agents, Samples 1, and 9-12 |
Control | |||||
Mixture# | 1 | 9 | 10 | 11 | 12 |
80% EPON Resin 828/20% | 100 | 100 | 100 | 100 | 100 |
HDDGE (diluent) mixture, | |||||
parts | |||||
Jeffamine D-230, parts | 18 | 6 | 6 | 6 | 6 |
IPDA, parts | 12 | 4 | 4 | 4 | 4 |
N-H/epoxy ratio | 1.00 | 0.33 | 0.33 | 0.33 | 0.33 |
DDMA, parts | 0 | 0 | 0 | 0 | 0 |
DMA, parts | 0 | 0 | 0 | 0 | 0 |
DMAEE, parts | 0 | 0 | 0 | 0 | 0 |
TMG, parts | 0 | 2.6 | 5.2 | 0 | 0 |
1-Bz-2-MI, parts | 0 | 0 | 0 | 4.2 | 8.3 |
Tg, ° C., after cure time at | |||||
70° C.: | |||||
2 hours | 51 | 41 | 51 | 51 | 56 |
3 hours | 65 | 55 | 81 | 55 | 86 |
4 hours | 72 | 71 | 83 | 79 | 91 |
5 hours | 77 | 85 | 86 | 81 | 90 |
6 hours | 80 | 95 | 85 | 96 | |
6 hours (repeat cure) | 77 | 82 | 90 | 88 | 97 |
Tg, ° C., after 6 hours at | 88.5 | 92 | 81 | 113 | 105 |
70° C. cure and after 30 | |||||
min at 200° C.: | |||||
Max peak exotherm temp | 261 | 240 | 299 | 266 | 307 |
at center, ° C.* | |||||
Time to max peak temper- | 18 | 38 | 38 | 28 | 24 |
ature, min* | |||||
Viscosity, Brookfield, | 203 | N/A | N/A | 399 | 360 |
30° C., mPa-s (cp) | |||||
Yield strength, MPa | 66.2 | N/A | N/A | N/A | N/A |
Break strength, MPa | N/A | N/A | N/A | N/A | N/A |
Modulus, MPa | 2953 | N/A | N/A | N/A | N/A |
Yield strain, % | 4.5 | N/A | N/A | N/A | N/A |
Break strain, % | 9.7 | N/A | N/A | N/A | N/A |
*Cure on 100 gram mass in 70° C. water bath. |
TABLE 4 |
Effect of dodecyldimethylamine (DDMA) on uncured viscosity and cured Tg of resin systems |
cured with primary amines at a near stoichiometric ratio of N—H to epoxy group |
Mixture# |
1 | ||||||||
(control) | 2 | 3 | 4 | 5 | 6 | 7 | ||
81.5 |
100 | 100 | 100 | 100 | 100 | 100 | 100 |
826/18.5% | |||||||
BDDGE (diluent) | |||||||
mixture, parts |
Curing agent formulation: |
Jeffamine D-230, | 20.48 | 20.48 | 20.48 | 19.44 | 19.44 | 18.46 | 18.46 |
parts | |||||||
IPDA, parts | 10.92 | 10.92 | 10.92 | 10.47 | 10.47 | 9.94 | 9.94 |
DDMA, |
0 | 1.00 | 2.00 | 1.00 | 2.00 | 2.00 | 3.00 |
N—H/epoxy ratio | 0.991 | 0.991 | 0.991 | 0.95 | 0.95 | 0.902 | 0.902 |
Viscosity, | 198.7 | 183.5 | 174.7 | 191.0 | 177.7 | 185.0 | 174.2 |
Brookfield, 25° C., | |||||||
mPa-s (cp) | |||||||
Time to 1 Pa-s | 162.5 | 136 | N/A | N/A | 148.5 | 151.5 | N/A |
viscosity at 30° C., | |||||||
min. | |||||||
Tg, ° C., after 6 hours | 73.6 | 77.2 | 77.6 | 76.8 | 77.9 | 79.0 | 77.8 |
at 70° C.: | |||||||
Tg, ° C., after 6 hours | 87.0 | 86.6 | 80.8 | 88.3 | 83.1 | 85.7 | 80.6 |
at 70° C. and 30 min | |||||||
at 180° C.: | |||||||
Max peak exotherm | 272 | 269 | N/A | N/A | 266 | 264 | N/A |
temp at center, ° C.* | |||||||
Time to max peak | 13 | 13 | N/A | N/A | 14 | 13 | N/A |
temperature, min.* | |||||||
*Cure on 100 gram mass in 70° C. water bath. |
TABLE 5 |
Effect of dodecyldimethylamine (DDMA) on uncured viscosity and cured Tg of BPA/BPF |
resin systems cured with primary amines at a near/stoichiometric ratio of N—H to epoxy |
Mixture# |
1 | ||||||||||
|
2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | ||
Resin formulation: |
EPON Resin | 48.9 | 48.9 | 48.9 | 0 | 0 | 0 | 0 | 0 | 0 |
828, | |||||||||
EPON Resin | |||||||||
0 | 0 | 0 | 65.2 | 65.2 | 65.2 | 54.6 | 54.6 | 54.6 | |
827, parts | |||||||||
EPON Resin | 32.6 | 32.6 | 32.6 | 16.3 | 16.3 | 16.3 | 26.9 | 26.9 | 26.9 |
862, parts | |||||||||
BDDGE, parts | 18.5 | 18.5 | 18.5 | 18.5 | 18.5 | 18.5 | 18.5 | 18.5 | 18.5 |
Curing agent formulation: |
Jeffamine D- | 20.41 | 20.41 | 18.39 | 20.54 | 20.54 | 18.46 | 20.67 | 20.67 | 18.59 |
230, parts | |||||||||
IPDA, parts | 10.99 | 10.99 | 9.91 | 11.06 | 11.06 | 9.94 | 11.13 | 11.13 | 10.01 |
DDMA, |
0 | 1.00 | 2.00 | 0 | 1.00 | 2.00 | 0 | 1.00 | 2.00 |
NH/epoxy ratio | 0.999 | 0.999 | 0.901 | 1.001 | 1.000 | 0.899 | 0.999 | 0.999 | 0.899 |
Viscosity, | 208.5 | 193.8 | 200.7 | 198.9 | 185.1 | 193.5 | 190.5 | 179.1 | 186.0 |
Brookfield, | |||||||||
25° C., mPa-s | |||||||||
(cp) | |||||||||
Tg, ° C., after 6 | 68.37 | 70.58 | 74.58 | 71.6 | 73.3 | 76.31 | 65.44 | 72.5 | 75.05 |
hours at 70° C.: | |||||||||
Tg, ° C., after 6 | 79.72 | 81.57 | 81.39 | 80.49 | 81.7 | 83.07 | 80.47 | 81.09 | 81.98 |
hours at 70° C. | |||||||||
and 30 min at | |||||||||
180° C.: | |||||||||
TABLE 6 | |
Property Test |
DDMA | DDMA | |||
Control | Control | based | based | |
|
|
|
|
|
Resin System | Resin | Resin | Resin | Resin |
Mixture R | Mixture R | Mixture R | Mixture R | |
Curing | Curing | Curing | Curing | |
Agent C | Agent C | Agent C | Agent C | |
DDMA | DDMA | |||
Mix Ratio (parts by wt) | 100:30 | 100:30 | 100:15:6 | 100:15:6 |
|
75° C. at | 75° C. at | 72° C. and | 75° C. at |
5 hours | 8.3 |
75° C. each | 7.5 hours | |
at 3 hours | ||||
Transverse Tensile | 29.9 | 25.5 | 51.1 | 53.7 |
Strength (TTS) MPa-1st | ||||
break | ||||
TTS Strain-1st break, % | 0.25 | 0.25 | 0.56 | 0.51 |
0° Flex Strength MPa | 813 | 852 | 1015 | 998 |
0° Flex Modulus GPa | 32.7 | 33.7 | 33.9 | 35 |
In-Plane Shear Strength | 54.7 | N/A | 62 | N/A |
(+−45 tensile), |
||||
1. Resin Mixture R contains 80% by weight |
||||
2. Curing Agent mixture C contains 60% by weight Jeffamine ™ D-230 and 40% by weight of isophoronediamine (IPDA). |
Claims (24)
Priority Applications (2)
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US15/674,060 Active US9920161B2 (en) | 2010-06-24 | 2017-08-10 | Epoxy systems for composites |
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CN102432838A (en) | 2012-05-02 |
DK2433985T3 (en) | 2020-06-15 |
RU2011125990A (en) | 2012-12-27 |
EP2433985A2 (en) | 2012-03-28 |
CA2743800A1 (en) | 2011-12-24 |
US9920161B2 (en) | 2018-03-20 |
ES2795830T3 (en) | 2020-11-24 |
BRPI1102649B1 (en) | 2020-11-24 |
BRPI1102649A2 (en) | 2012-11-20 |
EP2433985B1 (en) | 2020-04-01 |
CA2743800C (en) | 2015-01-13 |
CN102432838B (en) | 2015-05-06 |
US20110319564A1 (en) | 2011-12-29 |
RU2487148C2 (en) | 2013-07-10 |
EP2433985A3 (en) | 2015-12-09 |
US20160244552A1 (en) | 2016-08-25 |
MX2011006417A (en) | 2012-01-02 |
US20170335050A1 (en) | 2017-11-23 |
PT2433985T (en) | 2020-06-18 |
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